Sulfuric Acid → Cyclododecanone

Participants

Reaction Conditions

Reaction Steps

Cyclododecane (1.66 g; 9.88 mmol), t-butylnitrite (2 mmol), N-hydroxyphthalimide (0.4 mmol), and acetic acid (2 ml) were placed in a flask and were stirred at 80° C. in an atmosphere of argon gas for 1 hour. The mixture was further treated with fuming sulfuric acid having a concentration of 5% by weight (100 mg) with stirring at 70° C. for 15 minutes under anhydrous conditions. The reaction mixture was neutralized with sodium hydroxide and was analyzed to find that cyclododecanone oxime, nitrocyclododecane, and cyclododecanone were formed in yields of 48%, 6%, and 3%, respectively.

Provenance & Evidence